Toward Perylene Dyes by the Hundsdiecker Reaction

Zagranyarski, Yulian; Chen, Long; Jänsch, Daniel; Geßner, Thomas; Li, Chen; Müllen, Kläus

doi:10.1021/ol5008586

Cited by 51 publications

(67 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Rylenes can also be regarded as a narrow GNR, and this relation could be further corroborated by a chemical reaction, the Hundsdiecker decarboxylation. 64 Thereby, PDIs were transformed into tetrabromo perylenes 16 (Scheme 7). These compounds were used by Lifeng Chi and Harald Fuchs as unique building blocks for GNR 16a formation on gold surfaces.…”

Section: Scheme 5: Synthesis Of Graphene Nanoribbons In Solutionmentioning

confidence: 99%

Evolution of Graphene Molecules: Structural and Functional Complexity as Driving Forces behind Nanoscience

2014

Self Cite

View full text Add to dashboard Cite

Abstract:The evolution of nanoscience is based on the ability of the fields of chemistry and physics to share competencies through mutually beneficial collaborations. With this in mind, in this Perspective, I describe three classes of compounds: rylene dyes, polyphenylene dendrimers, as well as nanographene molecules and graphene nanoribbons, which have provided a superb platform to nurture these relationships. The synthesis of these complex structures is demanding, but also rewarding because they stimulate unique investigations at the singlemolecule level by scanning tunneling microscopy and single-molecule spectroscopy. There are close functional and structural relationships between the molecules chosen. In particular, rylenes and nanographenes can be regarded as honeycombtype, discoid species composed of fused benzene rings. The benzene ring can thus be regarded as a universal modular building block. Polyphenylene dendrimers serve, first, as a scaffold for dyes en route to multichromophoric systems and, second, as chemical precursors for graphene synthesis. Through chemical design, it is possible to tune the properties of these systems at the single-molecule level and to achieve nanoscale control over their self-assembly to form multifunctional (nano)materials.

show abstract

Section: Scheme 5: Synthesis Of Graphene Nanoribbons In Solutionmentioning

confidence: 99%

Evolution of Graphene Molecules: Structural and Functional Complexity as Driving Forces behind Nanoscience

2014

Self Cite

View full text Add to dashboard Cite

show abstract

“…The absorption spectrum of 5‐OMe is slightly blue‐shifted compared to that of 5 , and shows an even larger split width of the Q‐like bands (6029 cm −1 ; Figure ). Such significant bathochromic shifts in the absorption spectra of 5 and 5‐OMe are also observed in those of disulfide‐appended polyaromatic hydrocarbons . These perturbations in the absorption spectrum of 5 are completely lost in the absorption spectrum of S,S ‐dioxodithiazolosubporphyrin 8 that shows almost the same spectral features as those of 1 .…”

Section: Resultsmentioning

confidence: 97%

Pyrrole‐Modified Subporphyrins Bearing a Sulfur‐Containing Heterocyclic Unit

Yoshida

Osuka

2018

Helvetica Chimica Acta

View full text Add to dashboard Cite

As new pyrrole‐modified subporphyrins (PMSubPs) bearing a sulfur‐containing heterocyclic unit, dithiazolosubporphyrin 5, dithiazinosubchlorin 6, and oxodithiazinosubchlorin 7 were synthesized from α‐fluorosubchlorophin 2 via α’‐selective nitration with Cu(NO3)2 followed by double SN2 reaction with methyl 3‐mercaptopropionate as a key step. Oxidation of 5 with H2O2 in the presence of a tungsten catalyst afforded S,S‐dioxodithiazolosubporphyrin 8 and nitration of 5 with Cu(NO3)2·3H2O gave β‐nitrodithiazolosubporphyrin 9 or β,β‐dinitrodithiazolosubporphyrins 10a and 10b depending on reaction conditions. In the solid‐states, the dithiazole units in 8 and 9 are almost planar but the dithiazine unit in 6 and the 2‐oxodithiazine unit in 7 are non‐planar. Compared to subchlorophin 1, dithiazolosubporphyrin 5 possesses a significantly reduced diatropic ring current and a greatly perturbed absorption spectrum showing largely split Q‐like bands at 501 and 660 nm. These perturbed electronic and optical properties of 5 are considerably attenuated in 6 and 7 and completely vanished in 8, suggesting the importance of disulfide bond for the large perturbation.

show abstract

“…In order to calculate the absolute energies of LUMO level with respect to the vacuum level, the redox data are standardized to the ferrocene/ferricenium couple which has a calculated absolute energy of -4.8 eV 32 . The data related to LUMO level energies of dyes are presented in Table 3.…”

Section: Lowest Unoccupied Molecular Orbital (Lumo)mentioning

confidence: 99%

“…Highest occupied molecular orbital (HOMO) Table 4 depicts the highest occupied molecular orbital energy levels, which are calculated using the standard reported procedure [32]. Considering the energy range from -6.64 to -7.54 eV for xanthene dyes 3a-e and 6a-e, it is observed that for dyes 3a and 6a HOMO energy levels are at very low energy carboxylic groups present in the xanthene chromophore while 6b and 6e have high HOMO energy levels due to the mesomorphic and the inductive effect of hydroxyl groups present in dye molecule.…”

Section: Band Gap Energy (Eg)mentioning

confidence: 99%

Solvent Free, One Pot Synthesis of Symmetric Xanthene Dyes and Their Electrochemical Study

Shabir

Saeed

2016

J. Chil. Chem. Soc.

View full text Add to dashboard Cite

The present paper reports the synthesis of xanthene dyes derivatives from 4, 4'-oxydiphthalic anhydride and 1, 4, 5, 8-naphthalenetetracarboxylic dianhydride (3a-e and 6a-e) with different substituted phenols via Friedel-Crafts acylation reaction in the presence of an ammonium chloride catalyst. The structures of all newly synthesized derivatives were confirmed by the chromatographic, spectral and microelemental data. Dianhydride derivatives with 3-N', N'-dimethylaminophenol (3d and 6d) and resorcinol (3e and 6e) have been found to be highly fluorescent. Electrochemical study was done to determine band gap energy, LUMO and HOMO level energy. Band gap and LUMO energy levels were found to be lowest in xanthene derivatives 3c and 6c. Dyes 3d, 3e, 6d and 6e were found useful for differential staining of plant cells.

show abstract

Toward Perylene Dyes by the Hundsdiecker Reaction

Cited by 51 publications

References 24 publications

Evolution of Graphene Molecules: Structural and Functional Complexity as Driving Forces behind Nanoscience

Evolution of Graphene Molecules: Structural and Functional Complexity as Driving Forces behind Nanoscience

Pyrrole‐Modified Subporphyrins Bearing a Sulfur‐Containing Heterocyclic Unit

Solvent Free, One Pot Synthesis of Symmetric Xanthene Dyes and Their Electrochemical Study

Contact Info

Product

Resources

About